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Are the settings the same on the Mac and Windows boxes? I'm assuming that both the Dial-Up and Broadband connections are DHCP'ing an IP from the ISP. Maybe something set in the ISA server to allow specific IP address ranges, doubt it though.
Something has to be wrong with your routes if you're leaving after coming inside. Would just sit down with pen and paper and draw them out.
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"You hear the one about the fella who died, went to the pearly gates? St. Peter let him in. Sees a guy in a suit making a closing argument. Says, "Who's that?" St. Peter says, "Oh, that's God. Thinks he's Denny Crane."
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